Across disciplines, mid-career faculty may be motivated by internal and external factors to pursue financial support for their work. Yet, it is unclear how mid-career faculty navigate individualized realities to develop the necessary skills for success in this aspect of their careers. This chapter guides the reader through planning for the pursuit of funding at mid-career in ways that promote agency, vitality, and fulfillment. Rather than emphasizing strategies for securing grants, it focuses on a reflective practice that places at the foreground individual decision-making in alignment with personal goals, talents, and needed areas of development. The chapter includes an overview of challenges faced by mid-career faculty as well as growth-promoting models of academic careers, and then transitions to a reflective planning guide. It concludes with recommendations for key stakeholders in support of mid-career faculty.